Benzyl Bromide → Benzenemethanamine, N,N-diethyl-

HRID 329658

Reaction equation

HRID 329658 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>CCOCC>[CH2:9]([N:11]([CH2:12][CH3:13])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 8021Diethylamine

Product 1

HCID 61211Benzenemethanamine, N,N-diethyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 11.9 ml of benzyl bromide in 100 ml of ether was added dropwise to a mixture of 30.9 ml of diethylamine in 100 ml of ether. This mixture was stirred overnight then filtered and washed with ether. The combined filtrate and wash was washed with water, dried and concentrated to an oil. This oil was distilled through a Kugelrohr and the fraction boiling at <70° C., 1.5 mm collected, giving 10.6 g of N,N-diethylbenzenemethanamine as an oil.

Workup

  1. filtrationthen filtered
  2. washwashed with ether
  3. washThe combined filtrate and wash
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated to an oil
  7. distillationThis oil was distilled through a Kugelrohr
  8. customthe fraction boiling at <70° C., 1.5 mm collected

Sources & evidence

ORD record
ord-c99b104171c84824b229bcb5f824dde4
Source dataset
uspto-grants-1990_01
Patent number
US04892885

Linked notes

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